(Co)polymers based on vinyl units and use thereof in electroluminescent arrangements

- Bayer AG

This invention relates to (co)polymers which contain at least one repeat chain unit of the general formula (1) or (2) and optionally repeat units of the general formula (3), ##STR1## in which L.sup.1 and L.sup.2 denote a photoluminescent residue,wherein the proportion of structural units of the formulae (1) and/or (2) is in each case 0.5 to 100 mol. % and of (3) is 0 to 99.5 mol. % and the molar percentages add up to 100,to the use thereof for the production of electroluminescent arrangements and to the electroluminescent arrangements.

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Claims

1. (Co)polymers which contain at least one repeat chain unit of the general formula (1) or (2) and optionally repeat units of the general formula (3), ##STR38## in which R.sup.1, R.sup.2 and R.sup.3 mutually independently mean hydrogen or C.sub.1 -C.sub.6 alkyl,

M denotes CN or C.sub.1 -C.sub.30 alkoxycarbonyl, C.sub.1 -C.sub.30 (di)alkylaminocarbonyl, C.sub.1 -C.sub.30 alkylcarbonyl, which may each be substituted by hydroxy or C.sub.1 -C.sub.6 alkoxycarbonyl, and furthermore denotes phenyl, naphthyl, anthracenyl, pyridyl or carbazolyl, which may each be substituted by residues selected from the group consisting of halogen, hydroxy, silyl, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.1 -C.sub.30 alkoxy, C.sub.1 -C.sub.30 alkoxycarbonyl, C.sub.1 -C.sub.30 acyloxy and C.sub.1 -C.sub.30 alkylcarbonyl,
L.sup.1 and L.sup.2 each denote a photoluminescent residue,

2. (Co)polymers according to claim 1, wherein L.sup.1 and L.sup.2 mutually independently denote a photoluminescent residue which is based on the skeleton of a fluorescent dye which is selected from the group consisting of:

coumarins of the formula (4) ##STR39## where X.sup.1.dbd.O or S, ##STR40## where X.sup.2.dbd.NR.sup.23, CH.sub.2, S or O, wherein R.sup.23 denotes hydrogen or C.sub.1 -C.sub.6 alkyl, oxazoles, or 1, 3, 4-oxadiazoles of the formula (11) ##STR41## where X.sup.3.dbd.CH or N ##STR42## where X.sup.4.dbd.O, S, Se or CH.sub.2, wherein
R.sup.4 denoted hydrogen, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.24 aralkyl or C.sub.1 -C.sub.30 alkoxy or ##STR43## wherein R.sup.43 and R.sup.44 mutually independently denote hydrogen, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, or C.sub.7 -C.sub.24 aralkyl, which may each be substituted by hydroxy or C.sub.1 -C.sub.4 alkoxycarbonyl, or,
R.sup.43 and R.sup.44, together with the nitrogen atom to which they are attached, may mean a morpholine, piperidine, pyrrolidine or piperazine ring, which may bear one or two substituents selected from the group consisting of methyl, ethyl and phenyl,
R.sup.5 denotes hydrogen, cyano, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.34 aralkyl, C.sub.1 -C.sub.30 alkoxy, C.sub.2 -C.sub.12 acyl, C.sub.1 -C.sub.12 alkoxycarbonyl, or C.sub.1 -C.sub.12 (di)alkylaminocarbonyl,
R.sup.6 denotes hydrogen, cyano, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.34 aralkyl, C.sub.1 -C.sub.30 alkoxy or ##STR44## wherein Z denotes a group OR.sup.45 or ##STR45## and R.sup.45, R.sup.46 and R.sup.47 mutually independently denote C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl or C.sub.7 -C.sub.24 aralkyl, wherein the aromatic rings may additionally be substituted by halogen, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy,
R.sup.7, R.sup.8 and R.sup.9 mutually independently mean hydrogen, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.24 aralkyl, C.sub.1 -C.sub.30 alkoxy, cyano, C.sub.2 -C.sub.12 acyl, C.sub.1 -C.sub.12 alkoxycarbonyl, C.sub.1 -C.sub.12 (di)alkylaminocarbonyl or an amino group with one or two C.sub.1 -C.sub.6 alkyl groups,
R.sup.10 denotes hydrogen, cyano, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.24 aralkyl, C.sub.1 -C.sub.30 alkoxy, amino, an amino group with one or two C.sub.1 -C.sub.6 alkyl groups, C.sub.2 -C.sub.12 acyl, C.sub.1 -C.sub.12 alkoxycarbonyl or C.sub.1 -C.sub.12 (di)alkylaminocarbonyl,
R.sup.11 denotes hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 acyl, C.sub.8 -C.sub.24 aralkenyl, unsubstituted amino, or amino identically or differently mono- or disubstituted by, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl or C.sub.7 -C.sub.24 aralkyl,
R.sup.11 furthermore denotes morpholinyl, piperidinyl, pyrrolidinyl or piperazinyl, which may bear one or two substituents selected from the group consisting of methyl, ethyl and phenyl,
R.sup.12 denotes hydrogen, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.24 aralkyl or C.sub.1 -C.sub.30 alkoxy,
R.sup.13 denotes hydrogen, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.34 aralkyl, C.sub.1 -C.sub.30 alkoxy or ##STR46## wherein R.sup.49 and R.sup.50 mutually independently denote C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, or C.sub.7 -C.sub.24 aralkyl or,
R.sup.49 and R.sup.50, together with the nitrogen atom to which they are attached, denote morpholinyl, piperidinyl, pyrrolidinyl or piperazinyl, which may bear one or two identical or different substituents selected from the group consisting of methyl, ethyl and phenyl,
R.sup.14 and R.sup.15 mutually independently mean hydrogen, cyano, halogen, nitro, C.sub.1 -C.sub.30 alkyl, C.sub.1 -C.sub.30 alkoxy, C.sub.6 -C.sub.18 aryl or C.sub.7 -C.sub.24 aralkyl, C.sub.1 -C.sub.12 alkoxycarbonyl, C.sub.2 -C.sub.12 acyl, C.sub.1 -C.sub.12 (di)alkylaminocarbonyl, or C.sub.1 -C.sub.6 (di)alkylamino,
R.sup.17 and R.sup.23 denote hydrogen, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl or C.sub.7 -C.sub.24 aralkyl and
R.sup.16, R.sup.18 to R.sup.22, R.sup.24 to R.sup.40 mutually independently mean hydrogen, cyano, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.24 aralkyl, C.sub.1 -C.sub.30 alkoxy, an amino group with one or two C.sub.1 -C.sub.6 alkyl groups, unsubstituted amino, C.sub.2 -C.sub.12 acyl, C.sub.1 -C.sub.12 alkoxycarbonyl or C.sub.1 -C.sub.12 (di)alkylaminocarbonyl, wherein the aliphatic carbon chains in the residues R.sup.4 to R.sup.13, R.sup.16 to R.sup.40 may be interrupted by one or more heteroatoms selected from oxygen, nitrogen and sulphur and/or by one or more phenylene rings, which may be substituted by C.sub.1 -C.sub.4 alkyl and/or halogen,

3. (Co)polymers according to claim 1, wherein the proportion of the structural units of the formulae (l) and/or (2) is 0.5 to 60 mol. % and optionally that of the formula (3) is 40 to 99.5 mol. %.

4. (Co)polymers according to claim 1, wherein and L.sup.1 and L.sup.2 mutually independently denote a fluorescent dye residue selected from the group consisting of: coumarins of the formula (4), pyrenes of the formula (5), 1,8-naphthalimides of the formula (6), 1,8-naphthaloylene-1',2'-benzimidazoles of the formula (7), phenothiazines or phenoxazines of the formula (8), and carbazoles and fluorenes of the formula (10).

5. (Co)polymers according to claim 1, wherein said (co)polymers have the following formula (28) ##STR47## wherein Me=a methyl group and Et=an ethyl group.

6. (Co)polymers according to claim 1, wherein said (co)polymers have the following formula (31) ##STR48## wherein Me=a methyl group.

7. (Co)polymers according to claim 1, wherein said (co)polymers have the following formula (34) ##STR49## wherein Me=a methyl group.

8. (Co)polymers according to claim 2, in which L.sup.1 or L.sup.2 is a photoluminescent residue which has the structure ##STR50##

9. (Co)polymers according to claim 2, in which L.sup.1 or L.sup.2 is a photoluminescent residue which has the structure ##STR51##

10. (Co)polymers according to claim 2, in which L.sup.1 or L.sup.2 is a photoluminescent residue which has the structure ##STR52##

11. (Co)polymers according to claim 2, in which L.sup.1 or L.sup.2 is a photoluminescent residue which has the structure ##STR53##

12. (Co)polymers according to claim 2, in which L.sup.1 or L.sup.2 is a photoluminescent residue which has the structure ##STR54##

13. (Co)polymers according to claim 2, in which L.sup.1 or L.sup.2 is a photoluminescent residue which has the structure ##STR55##

14. (Co)polymers according to claim 2, in which L.sup.1 or L.sup.2 is a photoluminescent residue which is based on the skeleton of a fluorescent dye having the following formula (4a) ##STR56## wherein R.sup.43 and R.sup.44 mutually independently denote hydrogen, C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl or C.sub.7 -C.sub.24 aralkyl, which may each be substituted by hydroxy or C.sub.1 -C.sub.4 alkoxycarbonyl or

R.sup.43 and R.sup.44, together with the nitrogen atom to which they are attached, may mean a morpholine, piperidine, pyrrolidine or piperazine ring, which may bear one or two substituents selected from the group consisting of methyl, ethyl and phenyl, and
Z denotes a group OR.sup.45 or --NR.sup.46 R.sup.47, wherein
R.sup.45 means C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl or C.sub.7 -C.sub.24 aralkyl, which are each substituted by at least one hydroxy group and wherein the aromatic rings may additionally be substituted by halogen, C.sub.1 -C.sub.6 alkyl and/or C.sub.1 C.sub.6 alkoxy and
R.sup.46 and R.sup.47 mutually independently denote C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, or C.sub.7 -C.sub.24 aralkyl, each optionally hydroxy-substituted, wherein at least one of the residues R.sup.46 and R.sup.47 has a hydroxy group and wherein the aromatic rings may additionally be substituted by halogen, C.sub.1 -C.sub.6 alkyl and/or C.sub.1 -C.sub.6 alkoxy,

15. (Co)polymers according to claim 2, in which L.sup.1 or L.sup.2 is a photoluminescent residue which is based on the skeleton of a fluorescent dye having the following formula (7a-1) or formula (7b-1) ##STR57## wherein R.sup.49' and R.sup.50' mutually independently denote C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.24 aralkyl, which may be substituted by hydroxy, or

R.sup.49' and R.sup.50', together with the nitrogen atom to which they are attached, moreover denote morpholinyl, piperidinyl, pyrrolidinyl or piperazinyl, which may bear one or two identical or different substituents selected from the group consisting of methyl, ethyl and phenyl,

16. (Co)polymers according to claim 2, in which L.sup.1 or L.sup.2 is a photoluminescent residue which is based on the skeleton of a fluorescent dye having the following formula (6a) ##STR58## in which R.sup.11' denotes hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 acyl, C.sub.8 -C.sub.24 aralkenyl, unsubstituted amino or amino identically or differently mono- or disubstituted by C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.18 aryl, C.sub.7 -C.sub.24 aralkyl,

R.sup.11' furthermore denotes morpholinyl, piperidinyl, pyrrolidinyl or piperazinyl, which may bear one or two substituents selected from methyl, ethyl and/or phenyl,
R.sup.12' denotes hydrogen, C.sub.1 -C.sub.30 alkyl, C.sub.1 -C.sub.30 alkoxy, C.sub.6 -C.sub.18 aryl or C.sub.7 -C.sub.24 aralkyl, which may be mono- or polysubstituted by hydroxy,

17. (Co)polymers according to claim 2, wherein R.sup.23 is hydrogen or C.sub.1 -C.sub.4 alkyl.

18. (Co)polymers according to claim 2, wherein the aliphatic carbon chains in the residues R.sup.4 to R.sup.13 and R.sup.16 to R.sup.40 are alkyl, alkoxy, alkylamino or aralkyl.

19. (Co)polymers according to claim 2, wherein the aliphatic carbon chains in the residues R.sup.4 to R.sup.13 and R.sup.16 to R.sup.40 may be interrupted by one or two heteroatoms selected from oxygen, nitrogen and sulphur.

20. (Co)polymers according to claim 2, wherein the aliphatic carbon chains in the residues R.sup.4 to R.sup.13 and R.sup.16 to R.sup.40 may be interrupted by one or two phenylene rings.

Referenced Cited
U.S. Patent Documents
3330834 July 1967 Senshu
3408338 October 1968 Szita et al.
3821383 June 1974 Sestanj et al.
4254109 March 3, 1981 Sestanj
4539507 September 3, 1985 Vanslyke et al.
4598081 July 1, 1986 Efimov et al.
4720432 January 19, 1988 Vanslyke et al.
4769262 September 6, 1988 Ferrar et al.
4769292 September 6, 1988 Tang et al.
5077142 December 31, 1991 Sakon et al.
5235045 August 10, 1993 Lewis et al.
5286803 February 15, 1994 Lindsay et al.
5384378 January 24, 1995 Etzbach et al.
5414069 May 9, 1995 Cumming et al.
5420136 May 30, 1995 Lewis et al.
5587444 December 24, 1996 Uchida et al.
Foreign Patent Documents
0 206 322 December 1986 EPX
0 294 061 December 1988 EPX
0 387 715 September 1990 EPX
0 406 762 January 1991 EPX
0 443 861 August 1991 EPX
0 532 798 March 1993 EPX
0 564 224 October 1993 EPX
0 686 662 December 1995 EPX
0 728 775 August 1996 EPX
23 60 705 June 1975 DEX
WO 90/13148 November 1990 WOX
WO 92/03490 March 1992 WOX
WO 92/03491 March 1992 WOX
WO 92/16023 September 1992 WOX
Other references
Patent History
Patent number: 5807945
Type: Grant
Filed: Sep 23, 1996
Date of Patent: Sep 15, 1998
Assignee: Bayer AG (Leverkusen)
Inventors: Yun Chen (Krefeld), Rolf Wehrmann (Krefeld), Andreas Elschner (Mulheim), Ralf Dujardin (Willich)
Primary Examiner: Joseph L. Schofer
Assistant Examiner: Wu C. Cheng
Law Firm: Connolly & Hutz
Application Number: 8/716,727